Diisopropylethylamine → HCID 59341405, 화합물

HRID 15465

반응식

HRID 15465 반응식
[F:1][C:2]1[CH:3]=[C:4]([Br:14])[C:5]2[O:9][C:8]([C:10]([OH:12])=O)=[CH:7][C:6]=2[CH:13]=1.Cl.Cl.[NH2:17][C@@H:18]1[CH:23]2[CH2:24][CH2:25][N:20]([CH2:21][CH2:22]2)[CH2:19]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[N:20]12[CH2:25][CH2:24][CH:23]([CH2:22][CH2:21]1)[C@@H:18]([NH:17][C:10]([C:8]1[O:9][C:5]3[C:4]([Br:14])=[CH:3][C:2]([F:1])=[CH:13][C:6]=3[CH:7]=1)=[O:12])[CH2:19]2

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12494972(R)-(+)-3-Aminoquinuclidine DihydrochlorideHCID 179827017-Bromo-5-fluorobenzofuran-2-carboxylic acid

생성물 1

HCID 59341405HCID 59341405, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

143 mg (0.55 mmol) of 5-fluoro-7-bromo-1-benzofuran-2-carboxylic acid, 100 mg (0.50 mmol) of (R)-3-aminoquinuclidine dihydrochloride, 229.14 mg (0.6 mmol) of HATU, 234 mg (1.81 mmol) of N,N-diisopropylethylamine and 2.0 ml of DMF are reacted according to the general procedure (variant B). DMF is removed under reduced pressure and the crude product is dissolved in 1N aqueous sodium hydroxide solution. The aqueous phase is extracted with ethyl acetate and washed with saturated sodium chloride solution. The combined organic phases are dried over magnesium sulfate and the solvent is removed under reduced pressure using a rotary evaporator. The crude product is taken up in methanol and, together with acidic ion exchange resin (Dowex WX2-200), shaken for about 20 min. The loaded ion exchanger is washed three times with in each case 30 ml of methanol, then with water, again with methanol, with dichloromethane and finally again with methanol. The product is eluted with methanol/triethylamine 95:5. The solvent is removed under reduced pressure using a rotary evaporator. 181 mg (98% of theory) of the title compound are isolated.

후처리

  1. customDMF is removed under reduced pressure
  2. dissolutionthe crude product is dissolved in 1N aqueous sodium hydroxide solution
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. washwashed with saturated sodium chloride solution
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customa rotary evaporator
  8. washThe loaded ion exchanger is washed three times with in each case 30 ml of methanol
  9. washThe product is eluted with methanol/triethylamine 95:5
  10. customThe solvent is removed under reduced pressure
  11. customa rotary evaporator

출처 및 근거

ORD 기록
ord-06c64707877a43b9b2fe015c1c5950f0
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732477B2

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